Applicators, dispensers and methods for dispensing and applying adhesive material

ABSTRACT

An applicator/dispenser assembly for dispensing and/or applying an adhesive material comprises: a first body portion and a second body portion, at least one of the first and second body portions being movable relative to the other of the first and second body portions; a cavity in at least one of the first and second body portions; and a piercing or breaking member arranged on one of the first and second body portions. Movement of one of the first and second body portions relative to the other of the first and second body portions moves the piercing or breaking member into the cavity. When a container of adhesive material is at least partially disposed within the cavity, movement of one of the first and second body portions relative to the other moves the piercing or breaking member to rupture the container for dispensing and/or applying the adhesive material.

RELATED APPLICATION INFORMATION

This application is a continuation of U.S. patent application Ser. No.10/663,909, filed Sep. 17, 2003, which is a continuation-in-partapplication of U.S. patent application Ser. No. 10/359,699, filed Feb.7, 2003, both incorporated herein by reference in their entirety.

BACKGROUND OF THE INVENTION

This invention relates to applicators and/or dispensers for dispensingand/or applying an adhesive material, for example, a polymerizablemonomer compound such as a cyanoacrylate adhesive, particularly formedical use.

Numerous swabs, applicators, dispensers and kits for dispensing andapplying various materials, including adhesive materials, are known.However, these known arrangements possess various shortcomings that makethem undesirable in many applications.

Monomer and polymer adhesives are used in both industrial (includinghousehold) and medical applications. Included among these adhesives arethe 1,1-disubstituted ethylene monomers and polymers, such as theα-cyanoacrylates. Since the discovery of the adhesive properties of suchmonomers and polymers, they have found wide use due to the speed withwhich they cure, the strength of the resulting bond formed, and theirrelative ease of use. These characteristics have made theα-cyanoacrylate adhesives the primary choice for numerous applicationssuch as bonding plastics, rubbers, glass, metals, wood, and, morerecently, biological tissues.

Medical applications of 1,1-disubstituted ethylene monomer adhesivecompositions include use as an alternate or an adjunct to surgicalsutures and staples in wound closure as well as for covering andprotecting tissue wounds such as lacerations, abrasions, burns,stomatitis, sores, and other open surface wounds. When such an adhesiveis applied, it is usually applied in its monomeric form, and theresultant polymerization gives rise to the desired adhesive bond.

Applicators for dispensing a polymerizable and/or cross-linkablematerial, such as a 1,1-disubstituted ethylene formulation, aredisclosed in U.S. Pat. No. 5,928,611 to Leung and copending U.S. patentapplication Ser. No. 09/430,177, filed Oct. 29, 1999. In general, manydifferent 1,1-disubstituted ethylene formulations are known for variousapplications, for example, cyanoacrylate formulations used asfast-acting surgical adhesives, sealants, bioactive agent releasematrixes and implants utilized in medical, surgical and other in vivoapplications. Such formulations include those disclosed by Leung and thereferences cited therein.

However, due to the need to apply the adhesive in its monomeric form,and due to the rapid polymerization rate of the monomers, it has beenvery difficult to design effective and commercially viable applicatorsand/or dispensers. Such applicators and/or dispensers mustcounterbalance the competing requirements that the monomer notprematurely polymerize, that the monomer be easily applied, that themonomer polymerize at a desired rate upon application, and that thesanitary and/or sterile properties of the monomer and applicator—whetherreal or perceived—be maintained. This latter requirement, that theactual or perceived sanitary and sterile condition of the monomer andapplicator be maintained, is particularly important in medicalapplications, where the user and/or the patient desires a clean productso as not to introduce further bacteria or foreign matter into a woundsite.

A further problem in addressing the above requirements of adhesiveapplicators and/or dispensers is the need to provide a stable monomerproduct. Particularly in small quantities, cyanoacrylate monomers areprone to premature polymerization, which would render the productuseless. Thus, industrial production of monomeric adhesive compositionshas had to balance rapid cure rates and high bond strengths withshelf-life. The shelf-life of these adhesives is primarily related tostability (i.e., constancy of compositional nature), uncured physicalproperties, rate of cure of the adhesive, as well as final curedproperties of the composition. For example, the shelf-life of amonomeric α-cyanoacrylate composition may be measured as a function ofthe amount of time the composition can be stored before unacceptablelevels of polymerization, such as measured by viscosity increase, occur.Unacceptable levels are indicated by a level of polymerization productthat reduces the usefulness of the composition in the application forwhich it is produced.

Known devices fail to provide an applicator and/or dispenser that isoptimized for convenient dispensing and application of adhesivematerials on a variety of surfaces and structures. The known applicatorsare generally either optimized for delivery of other compositions or areinconvenient for use in conjunction with adhesives. Furthermore, suchconventional devices generally do not address the competing needs ofease of use and adhesive stability prior to application.

SUMMARY OF THE INVENTION

This invention addresses the above needs by providing applicators anddispensers that permit economical and efficient use of adhesivecompositions. In embodiments of this invention, applicators and/ordispensers are provided that are more user friendly. In embodiments ofthis invention, applicators and/or dispensers are provided that are moreergonomic. In embodiments of this invention, applicators and/ordispensers are provided whereby an amount of adhesive material may beconveniently applied. The applicators and/or dispensers can be eitherdisposable or reusable, depending on the desired application.

In embodiments, an applicator and/or dispenser is designed to facilitatemanipulation by hand for dispensing and/or applying an adhesive. Forexample, in embodiments of this invention, applicators and/or dispensersare provided that are pen-like, providing a familiar feel to the user.In embodiments, an applicator and/or dispenser is designed to be morecomfortable to the user, easier to grip and/or easier to operate.

In embodiments, an applicator and/or dispenser is designed to provideacceptable stability and shelf-life to the adhesive composition withoutthe need to add separate stabilizer materials to the polymerizablemonomer. Thus, in these embodiments, because the shelf-life is providedby the applicator and/or dispenser itself, the cure rate of the adhesivecomposition is not adversely affected, as in the case where one or morestabilizers are added. Accordingly, the need to apply separatepolymerization initiators or rate modifiers can be reduced or eveneliminated.

In other embodiments, an applicator and/or dispenser includes apolymerization initiator or accelerator for the adhesive material. Thepolymerization initiator or accelerator may be disposed in or on a tipor other part of the applicator. The polymerization initiator oraccelerator may be absorbed or adsorbed into a porous portion of theapplicator, may be coated on a surface of the applicator, or otherwiseincorporated into a portion of the applicator. The applicator and/ordispenser may also include a frangible barrier separating first andsecond compartments, for example, to keep the polymerization initiatoror accelerator separated from the adhesive material prior to use.

In particular, this invention is directed to an applicator/dispenser fordispensing and/or applying an adhesive material, comprising: a firstbody portion and a second body portion, at least one of the first andsecond body portions being movable relative to the other of the firstand second body portions; a cavity in or an open space between at leastone of the first and second body portions; and a piercing or breakingmember arranged on one of the first and second body portions, whereinmovement of one of the first and second body portions relative to theother of the first and second body portions moves the piercing orbreaking member into the cavity or open space. In various embodiments,the applicator/dispenser further comprises a container of adhesivematerial at least partially disposed within the cavity or open space,wherein movement of one of the first and second body portions relativeto the other of the first and second body portions moves the piercing orbreaking member to rupture the container.

In embodiments, the adhesive material comprises a polymerizable monomeradhesive material. In embodiments, the adhesive material comprises apolymerizable 1,1-disubstituted ethylene monomer formulation. In stillother embodiments, the adhesive material comprises a cyanoacrylateformulation.

In embodiments, an applicator/dispenser for a polymerizable monomericadhesive material includes a material that provides acceptable stabilityand shelf-life to the adhesive composition without the need to addseparate stabilizer materials to the polymerizable monomer. As notedabove, because the shelf-life is provided by the material of theapplicator and/or dispenser, the cure rate of the adhesive compositionis not adversely affected. Thus, the need to apply separatepolymerization initiators or rate modifiers can be reduced or eveneliminated.

In other embodiments, the applicator/dispenser includes a polymerizationinitiator or accelerator for the adhesive material.

In embodiments, the applicator/dispenser further comprises a pivotingconnection that movably connects the first and second body portions. Inembodiments, the first and second body portions may comprise a handleportion of the applicator/dispenser.

In other embodiments, the second body portion is rotatable relative tothe first body portion. In embodiments, the applicator/dispenser furthercomprises a camming surface arranged on one of the first and second bodyportions other than the one of the first and second body portions onwhich the piercing or breaking member is arranged, wherein rotation ofthe second body portion relative to the first body portion moves thepiercing or breaking member into the cavity by contacting the cammingsurface and the piercing or breaking member.

In embodiments, the applicator/dispenser further comprises: a bladderdisposed at least partially within the cavity or open space, at least aportion of the bladder being flexible; and a container of adhesivematerial disposed within the bladder and at least partially located inthe cavity or open space, wherein movement of one of the first andsecond body portions relative to the other of the first and second bodyportions moves the piercing or breaking member to rupture the container.In embodiments, the applicator/dispenser further comprises a plug memberat least partially disposed in an opening of the bladder, the plugmember being made of a material that is at least one of porous,absorbent and adsorbent in nature. In embodiments, the plug membercomprises an applicator tip.

In embodiments, the applicator/dispenser further comprises: a slideassembly having a plunger portion that is at least partially disposed inthe cavity and a slide portion that is at least partially disposedoutside the cavity, the slide assembly being slidably movable to movethe plunger portion toward a dispensing opening of the cavity; and anopening in at least one of the first and second body portions throughwhich the slide portion of the slide assembly extends. In embodiments,the applicator/dispenser further comprises: a container of adhesivematerial disposed in the cavity between the dispensing opening of thecavity and the plunger portion of the slide assembly, wherein movementof one of the first and second body portions relative to the other ofthe first and second body portions moves the piercing or breaking memberto rupture the container and movement of the slide member moves theplunger portion to dispense the adhesive material from the cavity oncethe container is ruptured.

In other embodiments, this invention is directed to a kit comprising: atleast one applicator/dispenser; and a plurality of containers ofadhesive material arranged to be placed at least partially in the cavityor open space of the at least one applicator/dispenser, wherein movementof one of the first and second body portions relative to the other ofthe first and second body portions moves the piercing or breaking memberto rupture one of the containers that is placed at least partially inthe cavity or open space. In embodiments, the kit further comprises aplurality of removable applicator tips. In embodiments, the kit furthercomprises a polymerization initiator or rate modifier for the adhesivematerial. In embodiments, at least two of the plurality of containerscontain different amounts of adhesive material. In other embodiments, atleast two of the plurality of containers contain a different adhesivematerial.

In other embodiments, this invention is directed to a method ofapplying/dispensing an adhesive material comprising: placing a containerof adhesive material at least partially into the cavity or open space ofan applicator/dispenser; moving one of the first and second bodyportions relative to the other of the first and second body portions tomove the piercing or breaking member to rupture the container; anddispensing the adhesive material from the cavity. In embodiments, themethod further comprises applying the dispensed adhesive to a substrateto be bonded.

Various other features and advantages of this invention will be apparentfrom the following detailed description of exemplary embodiments.

BRIEF DESCRIPTION OF THE DRAWINGS

Exemplary embodiments of this invention are described in detail below,with reference to the attached drawing figures, in which:

FIG. 1 is a perspective view of a first exemplary embodiment of thisinvention;

FIG. 2 is a perspective view of the exemplary embodiment of FIG. 1illustrating activation of the applicator/dispenser;

FIG. 3 is a perspective view of a bladder portion and an ampoule of theexemplary embodiment of FIG. 1;

FIG. 4 is a partial cross-sectional view of the exemplary embodiment ofFIG. 1;

FIG. 5 is a perspective view of a second exemplary embodiment of thisinvention;

FIG. 6 is a perspective view of the exemplary embodiment of FIG. 5illustrating activation of the applicator/dispenser;

FIG. 7 is a cross-sectional view of the exemplary embodiment of FIG. 5;

FIG. 8 is a perspective view of a slider assembly of the exemplaryembodiment of FIG. 5;

FIG. 9 is a partial cross-sectional view of the exemplary embodiment ofFIG. 5;

FIG. 10 is a perspective view of a third exemplary embodiment of thisinvention;

FIG. 11 is an exploded view of the exemplary embodiment of FIG. 10;

FIG. 12 is an enlarged, partial view of the exemplary embodiment of FIG.10;

FIG. 13 is a top perspective view of a fourth exemplary embodiment ofthis invention;

FIG. 14 is a bottom perspective view of the exemplary embodiment of FIG.13; and

FIG. 15 is an exploded view of the exemplary embodiment of FIG. 13.

FIG. 16 is another embodiment of FIG. 15.

DETAILED DESCRIPTION OF EXEMPLARY EMBODIMENTS

In embodiments of this invention, an applicator/dispenser is providedthat facilitates easy application of a desired quantity of polymerizableadhesive material. In embodiments, an amount of polymerizable adhesivematerial is prepackaged in the applicator dispenser in a frangibleampoule that is broken upon activation of the applicator/dispenser. Thefrangible ampoule may provide stability and/or shelf-life for the amountof polymerizable adhesive material.

FIGS. 1-4 illustrate a first embodiment of this invention, although thisinvention is in no way limited to the specific design depicted therein.As shown in FIGS. 1 and 2, an applicator/dispenser 100 is formed by afirst body portion 110 and a second body portion 120 that are movablerelative to one another. For example, in the embodiment shown, apivoting connection 130 is provided that allows the first body portion10 and the second body portion 120 to be moved from an open, spacedapart relative position, illustrated in FIG. 1, to a substantiallyclosed, adjacent position, illustrated in FIG. 2. The relative positionillustrated in FIG. 1 may be a “cocked” position in embodiments thathave an amount of polymerizable adhesive material prepackaged in theapplicator/dispenser 100.

The first body portion 110 and the second body portion 120 define aspace therebetween into which a bladder 140 may be fitted. As shown inFIGS. 1 and 2, the first body portion 110 has an opening 112 throughwhich a push button portion 142 of the bladder 140 may extend. Asexplained below, the push button portion 142 may be depressed by a userto dispense a desired quantity of polymerizable adhesive material fromthe applicator/dispenser 100, for example, through a detachable orreplaceable tip 150. A user's thumb or finger may be used to depress thepush button portion 142 while the applicator/dispenser 100 is held bythe first and second body portions 110, 120 as a handle. For example, auser may hold the applicator/dispenser 100 as a pen and press the pushbutton portion 142 with an index finger.

The first body portion 110 and the second body portion 120 define anopen space 115 therebetween into which a bladder 140 may be fitted. Asshown in FIGS. 1 and 2, the first body portion 110 has an opening 112through which a push button portion 142 of the bladder 140 may extend.As explained below, the push button portion 142 may be depressed by auser to dispense a desired quantity of polymerizable adhesive materialfrom the applicator/dispenser 100, for example, through a detachable orreplaceable tip 150. A user's thumb or finger may be used to depress thepush button portion 142 while the applicator/dispenser 100 is held bythe first and second body portions 110, 120 as a handle. For example, auser may hold the applicator/dispenser 100 as a pen and press the pushbutton portion 142 with an index finger.

The tip 150 may be designed to friction fit over an end portion 160 ofthe applicator/dispenser 100. Alternatively, the tip 150 may fitdirectly on the porous plug 170 that is situated in an open end of thebladder 140, as described below.

The first body portion 110, the second body portion 120, the bladder 140and/or the tip 150 may be made of any suitable material, preferably amaterial that promotes stability of the polymerizable adhesive materialto be dispensed so as to avoid premature polymerization.

The porous plug 170 may include a polymerization initiator or ratemodifier for the polymerizable adhesive material to be dispensed. Theporous plug 170 may be impregnated with the polymerization initiator orrate modifier, or may have the polymerization initiator or rate modifiercoated on a surface thereof.

FIG. 3 shows an exemplary embodiment of the bladder 140 removed from theapplicator/dispenser 100. As described above, the bladder 140 has anopen end 144 into which the porous plug 170 is fitted. At least the pushbutton portion 142 of the bladder 140 is made of a flexible material.The bladder 140 may be blow molded of a suitable rubber, silicone orplastic material, such as, for example, polyvinyl chloride,polyethylene, polyurethane, natural or nitril rubber, or any combinationthereof.

A frangible ampoule 146 containing an amount of polymerizable adhesive148 is disposed in the bladder 140. The frangible ampoule 146 may bemade of any suitable material, preferably a material that promotesstability and shelf-life of the polymerizable adhesive material 148. Forexample, the frangible ampoule 146 may be made of glass. Othermaterials, such as, a plastic material or pierceable metal, such asaluminum, may be used for the frangible ampoule 146. An example of asuitable ampoule that can be used in the dispenser/applicators of thepresent invention is disclosed in, for example, U.S. Pat. No. 5,928,611,the entire disclosure of which is incorporated herein by reference. Infact, where such an ampoule is used in the present invention, the entireampoule/applicator device may be used, which would thereby constitutenot only the ampoule 144, but also the porous plug 170. In suchembodiments, the dispensers/applicators of the present invention areparticularly suitable for dispensing or applying the adhesive containedin the DERMABOND® topical skin adhesive product, available from Ethicon(Somerville, N.J.).

FIG. 4 illustrates the bladder 140, the push button portion 142, thefrangible ampoule 146 and the porous plug 170 assembled and insertedinto the space between the first body portion 110 and the second bodyportion 120, with the porous plug 170 extending through an opening inthe end portion 160 of the applicator/dispenser 100. As shown in FIG. 4,the second body portion 120 includes a piercing or breaking member 122that extends inwardly from an inner surface thereof. The breaking member122 is located so that the frangible ampoule 146 is broken by thebreaking member 122 when the first and second body portions 110, 120 aremoved from the open position shown in FIG. 1 to the closed positionshown in FIG. 2. The first and second body portions 110, 120 act aslevers on the pivoting connection 130, thus providing a mechanicaladvantage to facilitate breakage of the frangible ampoule 146.

FIG. 4 illustrates the bladder 140, the push button portion 142, thefrangible ampoule 146 and the porous plug 170 assembled and insertedinto the open space 115 between the first body portion 110 and thesecond body portion 120, with the porous plug 170 extending through anopening in the end portion 160 of the applicator/dispenser 1.00. Asshown in FIG. 4, the second body portion 120 includes a piercing orbreaking member 122 that extends inwardly from an inner surface thereof.The breaking member 122 is located so that the frangible ampoule 146 isbroken by the breaking member 122 when the first and second bodyportions 110, 120 are moved from the open position shown in FIG. 1 tothe closed position shown in FIG. 2. The first and second body portions110, 120 act as levers on the pivoting connection 130, thus providing amechanical advantage to facilitate breakage of the frangible ampoule146.

In the embodiment shown, the breaking member 122 is situated remote fromthe push button portion 142 and near the open end 144 of the bladder140. This location causes the frangible ampoule 146 to be broken nearthe open end 144 of the bladder 140 to help ensure that thepolymerizable adhesive 148 will flow from the bladder 140 and that theflow is not impeded by larger fragments of the broken ampoule 146.Further, breaking the frangible ampoule 146 remote from the push buttonportion 142 may help to avoid fragments that could accidentally piercethe push button portion 142 and cut a user's thumb or finger. Althoughnot shown, the bladder 140 may be thicker or reinforced at the pushbutton 142 to prevent such an occurrence. Alternatively, the ampoule 146may be placed within a separate tube-like structure, such as a standardbutyrate tube, having a section removed, such as a partially opened end.Fragments of the broken ampoule 146 can be contained by the tube whileallowing the polymerizable adhesive 148 to flow from the tube and fromthe bladder 140.

The bladder 140 is designed to contain the polymerizable adhesive 148once the frangible ampoule 146 is broken. The polymerizable adhesive 148may be forced from the bladder 140 by depressing the push button portion142, displacing the polymerizable adhesive 148 and causing it to flowthrough the porous plug 170. The polymerizable adhesive 148 flowingthrough the porous plug 170 may be applied directly to a desired siteusing the porous plug 170 as an applicator tip. Alternatively, thedetachable or replaceable tip 150 may receive the polymerizable adhesive148 flowing through the porous plug 170 for application.

A controlled flow of the polymerizable adhesive 148 may be obtained byproviding a slow, but steady pressure on the bladder 140, for example,by depressing the push button portion 142 to a desired extent and/or adesired number of times. In embodiments, the volume displaced bydepressing the push button portion 142 may correspond to a desiredamount of the polymerizable adhesive 148 that is to be dispensed.

As noted above, the amount of polymerizable adhesive material 148 may beprepackaged in the applicator/dispenser 100. The applicator/dispenser100 may be disposable and discarded after the amount of polymerizableadhesive material 148 in the frangible ampoule 146 has been dispensed orotherwise been used (i.e., polymerized). Alternatively, the amount ofpolymerizable adhesive material 148 may be separate from theapplicator/dispenser 100 and supplied to the applicator/dispenser 100prior to use.

In embodiments, a user may be able to select from a variety of adhesivematerials and/or amounts by selecting a frangible ampoule and/or bladderassembly (bladder, ampoule and plug) to be installed in theapplicator/dispenser 100. For example, a kit may be provided thatincludes at least one applicator/dispenser 100 and a plurality offrangible ampoules 146 (or bladder assemblies). A plurality ofdetachable or replaceable tips 150 may also be included in the kit. Thekit may also include a cleaning agent, such as isopropyl alcohol orother chemical sterilants, such as gluteraldehyde. Parts of the kit,such as the frangible ampoules 146 (or bladder assemblies) may bepackaged separately, for example, in a blister pouch, and may beunpackaged and combined with the applicator/dispenser 100 as needed.

FIGS. 5-9 illustrate a second embodiment of this invention, althoughthis invention is in no way limited to the specific design depictedtherein. As shown in FIGS. 5 and 6, an applicator/dispenser 200 isformed by a first body portion 210 and a second body portion 220 thatare movable relative to one another. For example, in the embodimentshown, a pivoting connection 230 is provided that allows the first bodyportion 210 and the second body portion 220 to be moved from an openposition, illustrated in FIG. 5, to a substantially closed position,illustrated in FIG. 6. The open position illustrated in FIG. 5 may be a“cocked” position in embodiments that have an amount of polymerizableadhesive material prepackaged in the applicator/dispenser 200.

As shown in FIGS. 5 and 6, the first body portion 210 has an openingthrough which a slide button portion 242 of a slider assembly 240 mayextend. As explained below, the slide button portion 242 may be moved bya user to dispense a desired quantity of polymerizable adhesive materialfrom the applicator/dispenser 200, for example, through a porous plug270 or other suitable tip. A user's thumb or finger may be used to movethe slide button 242 while the applicator/dispenser 200 is held by thefirst and second body portions 210, 220 as a handle. For example, a usermay hold the applicator/dispenser 200 as a pen and push or slide forwardthe slide button 242 with an index finger. The first body portion 210may include one or more contours 212 for a user's thumb or finger.

The slide button 242 is not limited to the specific embodiment shownFIGS. 5-9. The slide button 242 may be formed by a lever or othersuitable mechanism, such as a syringe shaft, that is arranged to movethe plunger portion 244 forward.

FIG. 7 shows a cross-sectional view of the applicator/dispenser 200 withthe first and second body portions 210, 220 in the open position. Asshown, the first and second body portions 210, 220 define a chamber 260into which a frangible ampoule 280 containing an amount of polymerizableadhesive material 282 may be placed. As shown in FIG. 7, the first bodyportion 210 has an opening 214 through which the slide button portion242 of the slide assembly 240 may extend. In the embodiment shown, theopening 214 is an elongated slot that allows the slide assembly to movein an axial direction of the applicator/dispenser 200. Thus, asexplained below, the slide button portion 242 may be moved by a user tomove a plunger portion 244 of the slide assembly 240. Once the frangibleampoule 280 is broken by a piercing or breaking member 222 provided, forexample, on the second body portion 220, movement of the plunger portion244 toward the porous plug 270 will cause the polymerizable adhesivematerial 282 to be dispensed from the applicator/dispenser 200.

Although not shown, it should be understood that the second embodimentmay also include a detachable or replaceable tip as described above withrespect to the first embodiment.

FIG. 8 shows an exemplary embodiment of the slide assembly 240 removedfrom the applicator/dispenser 200. The slide button portion 242 and theplunger portion 244 are connected by an intermediate portion 246 of theslide assembly 240. The intermediate portion 246 should be sufficientlyrigid to carry the plunger portion 244 against any resistance caused bythe polymerizable adhesive material 282, contact between the plungerportion 244 and the chamber 260, and/or the broken ampoule 280. On theother hand, the slide button portion 242 may be made of a rubbermaterial or a plastic material that is comfortable and/or provides asuitable grip for a user's finger or thumb. The plunger portion 244 maybe made of a rubber material or a plastic material that will slidewithin the chamber 260 while providing a sufficient seal against theinner surface of the chamber 260 to prevent substantial leakage of thepolymerizable adhesive material 282 during use. Alternatively, theplunger portion 244 may be provided with one or more seal rings 248 of asuitable material. The slide button portion 242 and the intermediateportion 246 may be made of any variety of thermoplastics, such as ABS,polycarbonate, ULTEM™ and the like. The plunger portion 244 and/or theseal rings 248 may be made of any variety of rubbers, such as natural,nitril, polyisoprene and the like. A suitable lubricant may be providedto allow the plunger portion 244 and/or the seal rings 248 to slidewhile maintaining contact with the inside surface of the chamber 260.Preferably, the lubricant and the materials selected do not react withor cause premature polymerization of the adhesive material.

FIG. 9 illustrates the slide assembly 240, the slide button 242, theplunger portion 244 and the frangible ampoule 280 inserted into thechamber 260. As shown in FIG. 9, the piercing or breaking member 222extends inwardly from an inner surface of the second body portion 220.The breaking member 222 is located so that the frangible ampoule 280 isbroken by the breaking member 222 when the first and second bodyportions 210, 220 are moved from the open position shown in FIG. 5 tothe closed position shown in FIG. 6. The first and second body portions210, 220 act as levers on the pivoting connection 230, thus providing amechanical advantage to facilitate breakage of the frangible ampoule280.

As described above with respect to the first embodiment, once the firstand second body portions 210, 220 are moved to the closed position shownin FIG. 6 and the frangible ampoule 280 is broken, the first and secondbody portions 210, 220 may be prevented from accidentally returning tothe open position shown in FIG. 5.

Although the breaking member 222 is situated near an end of thefrangible ampoule 280 remote from the porous plug 270 in the embodimentshown, the breaking member 222 and frangible ampoule may be located sothat the frangible ampoule 280 will be broken near an end closer to theporous plug 270 to help ensure that the polymerizable adhesive 282 willnot impeded by larger fragments of the broken ampoule 280. Further,while the breaking member 222 is shown as single localized member, itshould be understood that the breaking member 222 may extend along aportion of or the entire ampoule 280 and/or may comprise a plurality ofbreaking members. Further, while the ampoule 280 is shown as a singleampoule, it should be understood that a plurality of ampoules may beprovided. For example, one ampoule may contain the adhesive materialwhile another ampoule contains a bioactive material, such as amedicament, or other material.

The chamber 260 is designed to contain the polymerizable adhesive 282once the frangible ampoule 280 is broken. The polymerizable adhesive 282may be forced from the chamber 260 by moving the slide button portion242 so that the plunger portion 244 of the slide assembly 240 displacesthe polymerizable adhesive 282 and causes it to flow through the porousplug 270. The polymerizable adhesive 282 flowing through the porous plug270 may be applied directly to a desired site using the porous plug 270as an applicator tip. Alternatively, a detachable or replaceable tip mayreceive the polymerizable adhesive 282 flowing through the porous plug270 for application.

A controlled flow of the polymerizable adhesive 282 may be obtained bymoving the slide button portion 242 to a desired extent. In embodiments,movement of the slide assembly 240 may create a pressure within thedispenser/applicator 200 to force the polymerizable adhesive 282 toflow.

As noted above, the amount of polymerizable adhesive material 282 may beprepackaged in the applicator/dispenser 200. The applicator/dispenser200 may be disposable and discarded after the amount of polymerizableadhesive material 282 in the frangible ampoule 280 has been dispensed orotherwise been used (i.e., polymerized). Alternatively, the amount ofpolymerizable adhesive material 282 may be separate from theapplicator/dispenser 200 and supplied to the applicator/dispenser 200prior to use.

In embodiments, a user may be able to select from a variety of adhesivematerials and/or amounts by selecting a frangible ampoule to beinstalled in the applicator/dispenser 200. For example, a kit may beprovided that includes at least one applicator/dispenser 200 and aplurality of frangible ampoules 280. A plurality of detachable orreplaceable tips may also be included in the kit.

FIGS. 10-12 illustrate a third embodiment of this invention, althoughthis invention is in no way limited to the specific design depictedtherein. As shown in FIGS. 10 and 11, an applicator/dispenser 300 isformed by a first body portion 310 and a second body portion 320 thatare movable relative to one another. For example, in the embodimentshown, the first body portion 310 may be formed by two pieces that fittogether to provide an open end 314, as shown in FIG. 11. The secondbody portion 320 is rotatably situated on the end 314 of the first bodyportion 310.

As shown in FIGS. 10 and 11, the first body portion 310 has an opening312 through which a push button portion 342 of the bladder 340 mayextend. As explained below, the push button portion 342 may be depressedby a user to dispense a desired quantity of polymerizable adhesivematerial from the applicator/dispenser 300, for example, through adetachable or replaceable tip 350. A user's thumb or finger may be usedto depress the push button portion 342 while the applicator/dispenser300 is held by the first body portion 310 as a handle. For example, auser may hold the applicator/dispenser 300 as a pen and press the pushbutton portion 342 with an index finger.

It should be understood that the detachable or replaceable tip 350 mayhave any desired configuration. The tip 350 may be selected for aparticular application, and is not limited to the tapered nozzle designshown. For example, the applicator tip may be a fibrous swab, a spongeswab, a foam swab, a brush, a spatula or the like. Any suitable tip,either known or hereafter developed, may be used with theapplicators/dispensers according to this invention.

The tip 350 may be designed to friction fit with the end 314 of thefirst body portion 310 of the applicator/dispenser 300. Alternatively,the tip 350 may fit directly on a porous plug 370 that is situated in anopen end of the bladder 340, as described below. Further, the tip 350may be non-detachable once the applicator/dispenser 300 has beenassembled, for example, by connecting to the end 314 of the first bodyportion 310.

The first body portion 310, the second body portion 320, the bladder 340and/or the tip 350 may be made of any suitable material, preferably amaterial that promotes stability of the polymerizable adhesive materialto be dispensed so as to avoid premature polymerization.

The porous plug 370 may include a polymerization initiator or ratemodifier for the polymerizable adhesive material to be dispensed. Theporous plug 370 may be impregnated with the polymerization initiator orrate modifier, or may have the polymerization initiator or rate modifiercoated on a surface thereof.

FIG. 11 shows an exploded view of the third exemplary embodiment. Asdescribed above with respect to the first embodiment, the bladder 340has an open end 344 into which the porous plug 370 is fitted. At leastthe push button portion 342 of the bladder 340 is made of a flexiblematerial. The bladder 340 may be blow molded of a suitable rubber orplastic material, such as, for example, polyvinyl chloride,polyethylene, polyurethane, natural rubber, nitril rubber, and the like.

A frangible ampoule 346 containing an amount of polymerizable adhesive348 is disposed in the bladder 340. The frangible ampoule 346 may bemade of any suitable material, preferably a material that promotesstability and shelf-life of the polymerizable adhesive material 348. Forexample, the frangible ampoule 346 may be made of glass. Othermaterials, such as, a plastic material or a pierceable metal material,such as aluminum, may be used for the frangible ampoule 346. Similar tothe embodiment of FIGS. 1-4, discussed above, an example of a suitableampoule that can be used in the dispenser/applicators of the presentinvention is disclosed in, for example, U.S. Pat. No. 5,928,611, theentire disclosure of which is incorporated herein by reference. In fact,where such an ampoule is used in the present invention, the entireampoule/applicator device may be used, which would thereby constitutenot only the ampoule 346, but also the porous plug 370. In suchembodiments, the dispensers/applicators of the present invention areparticularly suitable for dispensing or applying the adhesive containedin the DERMABOND® topical skin adhesive product, available from Ethicon(Somerville, N.J.).

The bladder 340, the push button portion 342, the frangible ampoule 346and the porous plug 370 may be assembled and inserted into the spacebetween the two pieces of the first body portion 310, with the porousplug 370 extending through the open end 314 of the first body portion310 and the second body portion 320 rotatably situated on the end 314 ofthe first body portion 310.

As shown in FIGS. 11 and 12, the end 314 of the first body portion 310includes a piercing or breaking member 316 that extends inwardly. Thebreaking member 316 is located so that the frangible ampoule 346 isbroken by the breaking member 316 when the first and second bodyportions 310, 320 are rotated relative to one another so that a cammingsurface or inclined ramp located on an inner surface of the second bodyportion 320 presses the breaking member 316 into the frangible ampoule346. Upon relative rotation, the camming surface or ramp contacts aportion of the breaking member 316 that extends beyond the outer surfaceof the end 314 and presses the breaking member 316 inwardly against thefrangible ampoule 346. The camming surface or ramp provides a mechanicaladvantage to facilitate breakage of the frangible ampoule 346.

The bladder 340 is designed to contain the polymerizable adhesive 348once the frangible ampoule 346 is broken. The polymerizable adhesive 348may be forced from the bladder 340 by depressing the push button portion342, displacing the polymerizable adhesive 348 and causing it to flowthrough the porous plug 370. The polymerizable adhesive 348 flowingthrough the porous plug 370 may be applied to a desired site using thetip 350.

A controlled flow of the polymerizable adhesive 348 may be obtained bydepressing the push button portion 342 to a desired extent and/or adesired number of times. In embodiments, the volume displaced bydepressing the push button portion 342 may correspond to a desiredmetered amount of the polymerizable adhesive 348 that is to bedispensed.

As noted above, the amount of polymerizable adhesive material 348 may beprepackaged in the applicator/dispenser 300. The applicator/dispenser300 may be disposable and discarded after the amount of polymerizableadhesive material 348 in the frangible ampoule 346 has been dispensed orotherwise been used (i.e., polymerized). Alternatively, the amount ofpolymerizable adhesive material 348 may be separate from theapplicator/dispenser 300 and supplied to the applicator/dispenser 300prior to use.

In embodiments, a user may be able to select from a variety of adhesivematerials and/or amounts by selecting a frangible ampoule and/or bladderassembly (bladder, ampoule and plug) to be installed in theapplicator/dispenser 300. For example, a kit may be provided thatincludes at least one applicator/dispenser 300 and a plurality offrangible ampoules 346 (or bladder assemblies). A plurality ofdetachable or replaceable tips 350 may also be included in the kit.

FIGS. 13-15 illustrate a fourth embodiment of this invention, althoughthis invention is in no way limited to the specific design depictedtherein. As shown in FIGS. 13-15, an applicator/dispenser 400 is formedby a first body portion 410 and a second body portion 420 that aremovable relative to one another. For example, in the embodiment shown,the first body portion 410 may be formed by two pieces that fit togetherto provide an open end 414, as shown in FIG. 15. The second body portion420 is rotatably situated on the end 414 of the first body portion 410.

As shown in FIGS. 13-15, the first body portion 410 has an opening 412through which a push button portion 442 of the bladder 440 may extend.As explained below, the push button portion 442 may be depressed by auser to dispense a desired quantity of polymerizable adhesive materialfrom the applicator/dispenser 400, for example, through a detachable orreplaceable tip (not shown). A user's thumb or finger may be used todepress the push button portion 442 while the applicator/dispenser 400is held by the first body portion 410 as a handle. For example, a usermay hold the applicator/dispenser 400 as a pen and press the push buttonportion 442 with an index finger.

The first body portion 410, the second body portion 420, and/or thebladder 440 may be made of any suitable material, preferably a materialthat promotes stability of the polymerizable adhesive material to bedispensed so as to avoid premature polymerization.

A porous plug 470 is situated in an open end of the bladder 440, asfurther described below. The porous plug 470 may include apolymerization initiator or rate modifier for the polymerizable adhesivematerial to be dispensed. The porous plug 470 may be impregnated withthe polymerization initiator or rate modifier, or may have thepolymerization initiator or rate modifier coated on a surface thereof.

FIG. 15 shows an exploded view of the fourth exemplary embodiment. Asdescribed above with respect to the first embodiment, the bladder 440has an open end 444 into which the porous plug 470 is fitted. At leastthe push button portion 442 of the bladder 440 is made of a flexiblematerial. The bladder 440 may be blow molded of a suitable rubber orplastic material, such as, for example, polyvinyl chloride,polyethylene, polyurethane, natural rubber, nitril rubber, and the like.

A frangible ampoule 446 containing an amount of polymerizable adhesive448 is disposed in the bladder 440. The frangible ampoule 446 may bemade of any suitable material, preferably a material that promotesstability and shelf-life of the polymerizable adhesive material 448. Forexample, the frangible ampoule 446 may be made of glass. Othermaterials, such as, a plastic material or a pierceable metal material,such as aluminum, may be used for the frangible ampoule 446. Similar tothe embodiment of FIGS. 1-4, discussed above, an example of a suitableampoule that can be used in the dispenser/applicators of the presentinvention is disclosed in, for example, U.S. Pat. No. 5,928,611, theentire disclosure of which is incorporated herein by reference. In fact,where such an ampoule is used in the present invention, the entireampoule/applicator device may be used, which would thereby constitutenot only the ampoule 446, but also the porous plug 470. In suchembodiments, the dispensers/applicators of the present invention areparticularly suitable for dispensing or applying the adhesive containedin the DERMABOND® topical skin adhesive product, available from Ethicon(Somerville, N.J.).

In the fourth embodiment, the ampoule 446 is surrounded by a tube 447.The tube 447 may be of any suitable material that is compatible with theparticular adhesive to be applied, such as, for example, buterate orpolyethylene, and may be selected based on a desired application.

As shown, the tube 447 has a hole 449 formed therein. When assembled,the tube 447 is positioned in the bladder 440 so that the hole 449 isplaced in communication with the interior of the push button portion 442of the bladder 440. As described below, this allows the depression ofthe push button 442 to apply pressure to expel the adhesive 448. Inembodiments, the tube 447 is fixed or bonded to the bladder 440 so thatthe hole 449 is maintained in a proper position.

The bladder 440, the push button portion 442, the frangible ampoule 446,the tube 447 and the porous plug 470 may be assembled and inserted intothe space between the two pieces of the first body portion 410, with theporous plug 470 extending through the open end 414 of the first bodyportion 410 and the second body portion 420 rotatably situated on theend 414 of the first body portion 410.

As shown in FIG. 15 and FIG. 16, and as described above with respect toFIGS. 11 and 12 of the third embodiment, the end 414 of the first bodyportion 410 includes a piercing or breaking member 416 that extendsinwardly. In the fourth embodiment, two breaking members 416 areprovided that may be positioned opposite each other. The breakingmembers 416 are located so that the frangible ampoule 446 is broken bythe breaking members 416 when the first and second body portions 410,420 are rotated relative to one another so that corresponding cammingsurfaces or inclined ramps 411 located on an inner surface of the secondbody portion 420 press the breaking members 416 into the frangibleampoule 446. Upon relative rotation, the camming surfaces or rampscontact a portion of the corresponding breaking members 416 that extendbeyond the outer surface of the end 414 and press the breaking members416 inwardly against the tube 447 to apply pressure on the frangibleampoule 446. The camming surfaces or ramps provide a mechanicaladvantage to facilitate breakage of the frangible ampoule 446. Further,because the breaking members 416 are positioned opposite each other, thefrangible ampoule 446 is held in place to facilitate breakage.

As shown in FIG. 14, the applicator/dispenser 400 has a visual indicator450 that allows a user to determine whether the applicator/dispenser 400has been activated. The visual indicator 450 may be a set of raisedfeatures, as shown, or any other suitable set of markings, that allow auser to identify when the first and second body portions, 410, 420 arerotated relative to each other. For example, the visual indicator 450may be initially aligned prior to activation of the applicator/dispenser400, as shown in FIG. 14. Relative rotation of the first and second bodyportions, 410, 420 is thus clearly indicated by the visual indicator 450no longer being aligned.

Alternatively or additionally, the visual indicator 450 may comprise asecond feature/marking or set of features/markings that indicate whenthe first and second body portions, 410, 420 are relatively rotated to aposition in which the ampoule 446 is broken by the breaking members 416.

In the fourth embodiment, the tube or second container 447 is designedto contain the polymerizable adhesive 448 once the frangible ampoule 446is broken. The polymerizable adhesive 448 may be forced from the tube447 by depressing the push button portion 442 of the bladder 440,applying pressure via the hole 449, displacing the polymerizableadhesive 448 and causing it to flow through the porous plug 470. Thepolymerizable adhesive 448 flowing through the porous plug 470 may thenbe applied to a desired site.

A controlled flow of the polymerizable adhesive 448 may be obtained bydepressing the push button portion 442 to a desired extent and/or adesired number of times. In embodiments, the volume displaced bydepressing the push button portion 442 may correspond to a desiredmetered amount of the polymerizable adhesive 448 that is to bedispensed.

As noted above, the amount of polymerizable adhesive material 448 may beprepackaged in the applicator/dispenser 400. The applicator/dispenser400 may be disposable and discarded after the amount of polymerizableadhesive material 448 in the frangible ampoule 446 has been dispensed orotherwise been used (i.e., polymerized). Alternatively, the amount ofpolymerizable adhesive material 448 may be separate from theapplicator/dispenser 400 and supplied to the applicator/dispenser 400prior to use.

In embodiments, a user may be able to select from a variety of adhesivematerials and/or amount by selecting a frangible ampoule, a tube and/orbladder assembly (bladder, ampoule, tube and plug) to be installed inthe applicator/dispenser 400. For example, a kit may be provided thatincludes at least one applicator/dispenser 400 and a plurality ofcontainers of adhesive material, such as frangible ampoules 446 (orbladder assemblies) as shown in FIG. 16.

By making portions of the applicators/dispensers of this invention of amaterial that tends to stabilize the adhesive monomer composition, it ispossible and preferred in embodiments of this invention that theadhesive composition does not include, or is substantially free of, oneor more stabilizer components such as are known and used in the art asadditives to the adhesive monomer composition. This may reduce, or eveneliminate, the need for a polymerization initiator or accelerator. Forexample, suitable materials include those disclosed in copending U.S.patent application Ser. No. 09/874,039, filed Jun. 6, 2001, which ishereby incorporated herein by reference in its entirety. For example,suitable materials may include halogenated and/or fluorinated materials.

Suitable applicator tips, either the replaceable tip or the porous plugas described above, for the applicators/dispensers of this inventioninclude swabs, brushes, spatulas, droppers, syringes, and the like. Anysuitable applicator tip can be used that allows for application of theadhesive composition to the desired site, and thus different applicatortips may be appropriate for different application methods. Theapplicator tip can have a variety of suitable shapes, including, but notlimited to, conical, cylindrical, chisel or polygonal shapes such asrectangular or trapezoidal. The length and size of the tip can be varieddepending on various application parameters. The tip may be detachablefrom the applicator body, or may be an integral part of the applicator.

The replaceable tip can be composed of any of a variety of materialsincluding polymerized materials such as plastics, foams, rubber,thermosets, films, or membranes. Additionally, the replaceable tip maybe composed of materials such as metal, glass, paper, ceramics,cardboard, and the like. The replaceable tip material may be porous,absorbent, or adsorbent in nature to enhance and facilitate applicationof the adhesive composition. In general, the only limitation on thematerials used to fabricate the tip is that the tip must be sufficientlycompatible with the composition to be dispensed that undesirable effectson the composition do not prevail during contact of the composition withthe tip. Thus, for example, according to embodiments of this inventionwhere the adhesive composition is packaged as already being absorbed oradsorbed into the tip, or in direct contact with the tip, the tip ispreferably made from a material that tends to stabilize, or at leastdoes not prematurely polymerize, the adhesive monomer composition. Wherethe tip is made from polymer materials, the polymer material can be thesame as or different from those specified above. Suitable designs fortips that may be used according to this invention are disclosed in, forexample, U.S. patent application Ser. No. 08/488,411, filed Jun. 7,1995, Ser. No. 09/069,979, filed Apr. 30, 1998, Ser. No. 09/069,875,filed Apr. 30, 1998, and Ser. No. 09/385,030, filed Aug. 30, 1999, theentire disclosures of which are incorporated herein by reference.

Furthermore, the tips of the dispensers/applicators of this inventioncan be provided in any of various sizes, depending on the desired use ofthe product. For example, a standard preferred swab size can be arectangular shape having a size of about 1.3 cm×1.0 cm×0.64 cm. However,larger or smaller sizes can be used, where the sizes are tailored to theshape of the tip and/or the amount of adhesive material to be appliedfor a given application. Thus, for example, where thedispenser/applicator is intended for applications requiring a largeamount of adhesive material, a larger (and/or more absorbent) tip can beused; whereas where the dispenser/applicator is intended forapplications requiring only a small amount of adhesive material, asmaller (and/or less absorbent) tip can be used. Tailoring the size orabsorbency/adsorbency of the tip to the amount of adhesive required canhelp prevent waste of adhesive material. For example, where a large tip(and large amount of adhesive) is used for a small adhesive application,the remaining adhesive in the tip is generally wasted due to prematurepolymerization of the adhesive in the tip.

In addition to a polymerization initiator or rate modifier, the tip mayinclude a medicament, an anesthetic and/or other material to be applied.

The applicators/dispensers of this invention may be used to apply thepolymerizable adhesive composition to a variety of substrates for thepurposes of protecting, sealing, and bonding surfaces together. Suitablesubstrates include, but are not limited to, metals, plastics, rubbers,wood, ceramics, fabrics, cement, paper, living tissue and the like. Forexample, the polymerizable and/or cross-linkable material may be usefulas tissue adhesives, sealants for preventing bleeding or for coveringopen wounds, systems for delivery of therapeutic or other bioactiveagents, and other biomedical applications. They find uses in, forexample, closing surgically incised or traumatically lacerated tissues;setting fractured bone structures; retarding blood flow from wounds;aiding repair and regrowth of living tissues; providing implantablematrixes for delivering bioactive agents; dressing burns; dressing skinor other superficial or surface wounds (such as abrasions, chaffed orraw skin, and/or stomatitis); protecting tissues prone to damage (e.g.,as artificial calluses); and providing structural implants.

The adhesive material, in embodiments, is preferably a monomeric(including prepolymeric) adhesive composition. In embodiments, themonomer is a 1,1-disubstituted ethylene monomer, e.g., anα-cyanoacrylate. Preferred monomer compositions of this invention, andpolymers formed therefrom, are useful as tissue adhesives, sealants forpreventing bleeding or for covering open wounds, and in other absorbableand non-absorbable biomedical applications. They find uses in, forexample, apposing surgically incised or traumatically lacerated tissues;retarding blood flow from wounds; drug delivery; dressing burns;dressing skin or other superficial or surface wounds (such as abrasions,chaffed or raw skin, and/or stomatitis); hernia repair; meniscus repair;and aiding repair and regrowth of living tissue. Other preferred monomercompositions of this invention, and polymers formed therefrom, areuseful in industrial and home applications, for example in bondingrubbers, plastics, wood, composites, fabrics, and other natural andsynthetic materials.

The monomer (including prepolymeric) adhesive composition may includeone or more polymerizable monomers. Preferred monomers that may be usedin this invention are readily polymerizable, e.g. anionicallypolymerizable or free radical polymerizable, or polymerizable byzwitterions or ion pairs to form polymers. Such monomers include thosethat form polymers, that may, but do not need to, biodegrade. Suchmonomers are disclosed in, for example, U.S. Pat. Nos. 5,328,687 and5,928,611 to Leung et al., U.S. patent application Ser. No. 09/430,177,filed on Oct. 29, 1999, and U.S. Pat. No. 6,183,593, which are herebyincorporated in their entirety by reference herein. Preferred monomersinclude 1,1-disubstituted ethylene monomers, such as α-cyanoacrylatesincluding, but not limited to, alkyl α-cyanoacrylates having an alkylchain length of from about 1 to about 20 carbon atoms or more,preferably from about 2 to about 12 or more preferably from about 3 toabout 8 carbon atoms. Other suitable monomers include, but are notlimited to, alkyl ester cyanoacrylate monomers, such as those disclosedin, for example, U.S. patent application Ser. No. 09/630,437, filed Aug.2, 2000, and Ser. No. 09/919,877, filed Aug. 2, 2001, the entiredisclosures of which are incorporated herein by reference.

The α-cyanoacrylates of this invention can be prepared according toseveral methods known in the art. U.S. Pat. Nos. 2,721,858, 3,254,111,3,995,641, and 4,364,876, each of which is hereby incorporated in itsentirety by reference herein, disclose methods for preparingα-cyanoacrylates.

As desired, the application according to this invention can include anyof a wide variety of additional materials, either mixed into thepolymerizable composition, or in a separate compartment from thepolymerizable composition. Examples of suitable additional materialsinclude, but are not limited to, plasticizing agents, thixotropicagents, thickeners, natural or synthetic rubbers, stabilizers, pHmodifiers, bioactive agents, cross-linking agents, chain transferagents, fibrous reinforcements, colorants, preservatives, formaldehydereducing or scavenging agents, flavorants, perfumes, mixtures thereof,and the like.

The adhesive material may optionally also include at least one otherplasticizing agent that assists in imparting flexibility to the polymerformed from the monomer. The plasticizing agent preferably containslittle or no moisture and should not significantly affect the stabilityor polymerization of the monomer. Examples of suitable plasticizersinclude but are not limited to tributyl citrate, acetyl tri-n-butylcitrate (ATBC), polymethylmethacrylate, polydimethylsiloxane,hexadimethylsilazane, isopropyl myristate, isopropyl palmitate, andothers as listed in U.S. patent application Ser. No. 09/471,392 filedDec. 23, 1999, the disclosure of which is incorporated in its entiretyby reference herein.

The adhesive material may also optionally include at least onethixotropic agent. Suitable thixotropic agents are known to the skilledartisan and include, but are not limited to, silica gels such as thosetreated with a silyl isocyanate, and optionally surface treated titaniumdioxide. Examples of suitable thixotropic agents and thickeners aredisclosed in, for example, U.S. Pat. No. 4,720,513, and U.S. patentapplication Ser. No. 09/374,207 filed Aug. 12, 1999, the disclosures ofwhich are hereby incorporated in their entireties by reference herein.

The adhesive material may optionally also include thickeners. Suitablethickeners may include poly(2-ethylhexyl methacrylate),poly(2-ethylhexyl acrylate) and others as listed in U.S. patentapplication Ser. No. 09/471,392 filed Dec. 23, 1999, and Ser. No.09/374,207, filed Aug. 12, 1999, the disclosures of which areincorporated by reference herein in their entirety.

The adhesive material may also optionally include at least one naturalor synthetic rubber to impart impact resistance. Suitable rubbers areknown to the skilled artisan. Such rubbers include, but are not limitedto, dienes, styrenes, acrylonitriles, and mixtures thereof. Examples ofsuitable rubbers are disclosed in, for example, U.S. Pat. Nos. 4,313,865and 4,560,723, the disclosures of which are hereby incorporated in theirentireties by reference herein.

The adhesive material may optionally also include one or morestabilizers, preferably both at least one anionic vapor phase stabilizerand at least one anionic liquid phase stabilizer. The composition mayoptionally also include, in addition to or in place of the anionicstabilizers, at least one free radical stabilizer. These stabilizingagents may inhibit premature polymerization. Suitable anionic and freeradical stabilizers may include those listed in U.S. patent applicationSer. No. 09/471,392 filed on Dec. 23, 1999, and Ser. No. 09/099,457,filed Jun. 18, 1998, the disclosures of which are incorporated byreference herein in their entirety.

However, as described above, a particular advantage of this invention,such as in embodiments where stabilizing materials are used, is thatseparate stabilizers can be omitted from the composition. Thus, inembodiments, the polymerizable composition preferably does not includeany, or at least substantially none, additional stabilizer.

The adhesive material may also include pH modifiers to control the rateof degradation of the resulting polymer, as disclosed in U.S. patentapplication Ser. No. 08/714,288, filed Sep. 18, 1996, the entiredisclosure of which is hereby incorporated by reference herein in itsentirety.

Adhesive materials of this invention may also include at least onebiocompatible agent effective to reduce active formaldehydeconcentration levels produced during in vivo biodegradation of thepolymer (also referred to herein as “formaldehyde concentration reducingagents”). Preferably, this component is a formaldehyde scavengercompound. Examples of formaldehyde scavenger compounds useful in thisinvention include sulfites; bisulfites; mixtures of sulfites andbisulfites, etc. Additional examples of formaldehyde scavenger compoundsuseful in this invention and methods for their implementation can befound in U.S. Pat. Nos. 5,328,687, 5,514,371, 5,514,372, 5,575,997,5,582,834 and 5,624,669, all to Leung et al., which are herebyincorporated herein by reference in their entireties.

To improve the cohesive strength of adhesives formed from the adhesivematerials of this invention, difunctional monomeric cross-linking agentsmay be added to the monomer compositions of this invention. Suchcrosslinking agents are known. U.S. Pat. No. 3,940,362 to Overhults,which is hereby incorporated herein in its entirety by reference,discloses exemplary cross-linking agents.

The adhesive materials of this invention may further contain fibrousreinforcement and colorants such as dyes, pigments, and pigment dyes.Examples of suitable fibrous reinforcement include PGA microfibrils,collagen microfibrils, and others as described in U.S. patentapplication Ser. No. 09/471,392 filed on Dec. 23, 1999, the disclosureof which is incorporated by reference herein in its entirety.

The polymerizable adhesive materials useful in this invention may alsofurther contain one or more preservatives, for prolonging the storagelife of the composition. Suitable preservatives, and methods forselecting them and incorporating them into adhesive compositions, aredisclosed in U.S. patent application Ser. No. 09/430,180, the entiredisclosure of which is incorporated herein by reference.

In embodiments of this invention, the adhesive material and/or parts ofthe applicator/dispenser may contain additional materials such as apolymerization initiator, accelerator, rate-modifier, and/orcross-linking agent for initiating polymerization and/or cross-linkingof the polymerizable monomer material. Such initiators, accelerators,rate-modifiers, and/or cross-linking agents can be included in theapplicator tip, in the adhesive material, and/or elsewhere, asappropriate.

In embodiments of this invention, particularly where the adhesivematerial is not in contact with the applicator tip prior to use, it ispossible to incorporate into the applicator tip additional components,such as polymerization initiators and/or accelerators, anesthetic,medicament or the like, or even any of the various additives describedabove with respect to the polymerizable adhesive. This is advantageous,for example, where additional initiator or accelerator may be necessaryto provide the desired cure rate of the adhesive once it is applied orwhere additional treatment is desired. Furthermore, this is advantageousin embodiments where additional stabilizers or polymerization inhibitorsmust be added to the adhesive composition in the assembly, so as toovercome the “cure speed loss” that often occurs when such stabilizingagents are added.

In embodiments, the initiator or accelerator material is an initiatorand/or a rate modifier for polymerization and/or cross-linking of apolymerizable monomer. As used herein, a polymerization initiator is anymaterial that causes a monomer composition applied to a substantiallydry tissue (i.e., substantially in the absence of plasma or like tissuefluids) to polymerize in less than 300 seconds at ambient temperature,for example, at approximately 21-25° C. Preferably, the initiator causesthe monomer composition to polymerize in less than 150 seconds atambient temperature, more preferably within 60, 90 or 130 seconds. Asused herein, a polymerization rate modifier is any material that changesthe rate at which a polymerizable monomer would polymerize in theabsence of that material. Preferably, the rate modifier accelerates therate of the polymerization reaction, although for particularlyfast-acting monomers it may decelerate that rate.

The material may be applied to the applicator tip, for example, byspraying, dipping, injecting, or brushing the applicator tip with aliquid medium containing the polymerization initiator or accelerator. Itis preferably applied to the tip by dipping or injecting. For example,it may be applied to the tip by pumping of the liquid medium, forexample, through a syringe, onto the tip. Methods of applying thepolymerization initiator or accelerator to an applicator tip aredescribed in more detail in U.S. Pat. No. 5,928,611 to Leung and U.S.patent application Ser. No. 09/069,979, filed Apr. 30, 1998, Ser. No.08/920,876, filed Aug. 29, 1997, and Ser. No. 09/430,177, filed Oct. 29,1999, the entire disclosures of which is incorporated herein byreference.

Particular initiators and accelerators for particular monomers may bereadily selected by one of skill in the art without undueexperimentation. Control of the molecular weight distribution of theapplied adhesive can be enhanced by selection of the concentration andfunctionality of the initiator or accelerator vis-a-vis the selectedmonomer. Suitable polymerization initiators and accelerators forcyanoacrylate compositions include, but are not limited to, detergentcompositions; surfactants, including nonionic surfactants such aspolysorbate 20 (e.g., Tween 20™; ICI Americas), polysorbate 80 (e.g.,Tween 80™; ICI Americas), and poloxamers; cationic surfactants such astetrabutylammonium bromide; anionic surfactants, including quaternaryammonium halides such as benzalkonium chloride or its pure components,and benzethonium chloride; stannous octoate (tin (II) 2-ethylhexanoate),and sodium tetradecyl sulfate; and amphoteric or zwitterionicsurfactants such as dodecyldimethyl(3-sulfopropyl)ammonium hydroxide,inner salt; amines, imines, and amides, such as imidazole, tryptamine,urea, arginine and povidine; phosphines, phosphites and phosphoniumsalts, such as triphenylphosphine and triethyl phosphite; alcohols suchas ethylene glycol; methyl gallate; inorganic bases and salts, such assodium bisulfite, magnesium hydroxide, calcium sulfate and sodiumsilicate; sulfur compounds such as thiourea and polysulfides; polymericcyclic ethers such as monensin, nonactin, crown ethers, calixarenes andpolymeric epoxides; cyclic and acyclic carbonates, such as diethylcarbonate; phase transfer catalysts such as Aliquat™ 336 (General Mills,Inc., Minneapolis, Minn.); organometallics; manganese acetylacetonate;radical initiators and radicals, such as di-t-butyl peroxide andazobisisobutyronitrile; and bioactive compounds or agents.

In preferred embodiments, the initiator may be a bioactive material,including quaternary ammonium halides such asalkylbenzyldimethylammonium chloride (benzalkonium chloride; BAC) itspure components, or mixtures thereof, especially those with an alkylcontaining 6-18 carbon atoms; benzethonium chloride; and salts ofsulfadiazine. Cobalt napthenate can be used as an accelerator forperoxide. Other suitable bioactive materials are disclosed in U.S. Pat.No. 5,928,611 to Leung and U.S. patent application Ser. No. 08/920,876,filed Aug. 29, 1997, Ser. No. 09/430,176 filed Oct. 29, 1999, and Ser.No. 09/430,177, filed Oct. 29, 1999, the entire disclosures of which isincorporated herein by reference.

The adhesive materials in this invention can also comprise a medicament.Inclusion of a medicament is often desirable in compositions intendedfor medical applications. The medicament can either be added to themonomer-containing adhesive composition prior to packaging, or,alternatively, to the applicator tip or other part. Thus, the medicamentmay be applied to a tissue prior to or simultaneously with applicationof the monomer-containing adhesive composition. In addition to servingits medicinal function, the medicament may be selected so that itfunctions in conjunction with the co-packaged polymerizable monomercomposition to initiate polymerization of the monomer or modify (e.g.,accelerate) the rate of polymerization for the monomer to form apolymeric adhesive. The proper combination of medicament andpolymerizable monomer can be determined easily by one of skill in theart. The medicament is supplied in an amount that will bepharmaceutically effective when applied topically (i.e., directly totissue).

Examples of such medicaments include, but are not limited toantibiotics, antimicrobials, antiseptics, bacteriocins, bacteriostats,disinfectants, steroids, anesthetics, fungicides, anti-inflammatoryagents, antibacterial agents, antiviral agents, antitumor agents, growthpromoters, and mixtures thereof.

Exemplary medicaments include, but are not limited to, quaternaryammonium halides such as benzalkonium chloride and benzethoniumchloride; chlorhexidine sulfate; gentamicin sulfate; hydrogen peroxide;quinolone thioureas; silver salts, including, but not limited to, silveracetate, silver benzoate, silver carbonate, silver chloride, silvercitrate, silver iodide, silver nitrate, and silver sulfate; sodiumhypochlorite; salts of sulfadiazine, including, but not limited tosilver, sodium, and zinc salts; and mixtures thereof.

Preferable medicaments are those that are anions or help in radicalgeneration or that are ion pairs or are themselves radicals.

In embodiments, the medicament is preferably a quaternary ammoniumhalide such as alkylbenzyldimethylammonium chloride (benzalkoniumchloride; BAC) with an alkyl containing 6-18 carbon atoms, its purecomponents, or mixtures thereof, or benzethonium chloride; or a salt ofsulfadiazine, such as a silver, sodium, or zinc salt.

The medicament can have a pharmaceutical effect only at the site ofapplication (i.e., limited to the tissue on/in which it is applied), orit can have a systemic effect (by systemic, it is not only meant thatthe medicament has an effect throughout the patient's body, but also ata specific site other than the site of application). In embodimentswhere the medicament is applied in an amount sufficient to show asystemic pharmaceutical activity, it can be absorbed, transported, orotherwise distributed to the site or sites within the patient where thepharmaceutical activity is desired, e.g., through the cardiovascular orlymph systems. The medicament may be in the form of a solid, such as apowder or a solid film, or in the form of a liquid, such as a watery,viscous, or paste-like material. The medicament may also be compoundedwith a variety of additives, such as surfactants or emulsifiers, andvehicles.

The polymerizable and/or cross-linkable material may be neat (noadditional compounds added) or in a solvent, emulsion or suspension.Suitable solvents according to this invention include alcohol, etheralcohol, hydrocarbons, halogenated hydrocarbons, ethers, acetals,ketones, esters, acids, sulfur- or nitrogen-containing organiccompounds, mixtures thereof and the like. Other suitable solvents aredisclosed in U.S. Pat. No. 5,130,369 to Hughes et al. and U.S. Pat. No.5,216,096 to Hattori et al., the entire disclosures of which areincorporated herein by reference. These solvents may be used eitherindependently or in combination of two or more. They may also be used inconjunction with water to the extent that the polymerizable and/orcross-linkable material is dissolved or suspended in such a mixture. Thetotal amount of solvent that may be incorporated into the polymerizableand/or cross-linkable material may be 0 to 99, preferably 1 to 50, andmore preferably 3 to 25 percent by weight. Selection of the amount will,of course, depend on the desired monomer and process conditions, andamounts outside these ranges may be acceptable.

In embodiments, the monomer composition and/or its packaging arepreferably sterilized. Sterilization of the monomer composition and/orits packaging can be accomplished by techniques known to one of ordinaryskill in the art, and is preferably accomplished by methods including,but not limited to, chemical, physical, and/or irradiation methods.Examples of chemical methods include, but are not limited to, exposureto ethylene oxide or hydrogen peroxide vapor. Examples of physicalmethods include, but are not limited to, sterilization by heat (dry ormoist) or retort canning. Examples of irradiation methods include, butare not limited to, gamma irradiation, electron beam irradiation, andmicrowave irradiation. A preferred method is electron beam irradiation,as described in U.S. patent application Ser. No. 09/025,472, filed onFeb. 18, 1998, the entire disclosure of which is incorporated herein byreference. The composition must show low levels of toxicity to livingtissue during its useful life. In preferred embodiments of thisinvention, the composition is sterilized to provide a SterilityAssurance Level (SAL) of at least 10⁻³. In embodiments, the SterilityAssurance Level may be at least 10⁻⁴, or may be at least 10⁻⁵, or may beat least 10⁻⁶. Further details of sterilization are disclosed inincorporated U.S. patent application Ser. No. 09/874,039.

It should be understood that the individual features of the variousexemplary embodiments may be included or excluded as desired for a givenapplication. As such, all possible combinations of the describedfeatures are considered to be encompassed by this invention.

Thus, while this invention has been described in terms of exemplaryembodiments, it is to be understood that this invention is not to belimited to the particular configuration of these embodiments. Oneskilled in the art will recognize that various modifications and/oralterations of these embodiments may be made while remaining within thescope of this invention.

1. An applicator/dispenser assembly for dispensing and/or applying anadhesive material, comprising: a first body portion and a second bodyportion, at least one of the first and second body portions beingrotatable relative to the other of the first and second body portions; apivoting connection that movably rotates the first and second bodyportions; an open space at least partially in and between the first andsecond body portions; a bladder disposed in the open space and acontainer of adhesive material at least partially disposed within thebladder; and a piercing or breaking member arranged on at least one ofthe first and second body portions, wherein movement of one of the firstand second body portions relative to the other of the first and secondbody portions by the pivoting connection moves the piercing or breakingmember into the open space to rupture the container.
 2. Theapplicator/dispenser assembly according to claim 1, further comprising aplug member disposed in an open end of the bladder.
 3. Theapplicator/dispenser assembly according to claim 1, wherein the firstand second body portions comprise a handle portion of theapplicator/dispenser.
 4. The applicator/dispenser assembly of claim 1,wherein the bladder has a push button portion that extends through anopening in at least one of the first and second body portions fordisplacing the adhesive after the container of adhesive material isruptured and the push button portion is depressed.
 5. A kit comprising:at least one applicator/dispenser for dispensing and/or applying anadhesive material comprising a first body portion and a second bodyportion; at least one of the first and second body portions beingrotatable relative to the other of the first and second body portions; apivoting connection that movably rotates the first and second bodyportions; an open space at least partially in and between the first andsecond body portions; a bladder disposed in the open space and acontainer of adhesive material at least partially disposed within thebladder; and a piercing or breaking member arranged on at least one ofthe first and second body portions; and wherein movement of one of thefirst and second body portions relative to the other of the first andsecond body portions by the pivoting connection moves the piercing orbreaking member into the open space to rupture the container.
 6. The kitaccording to claim 5, further comprising at least one removableapplicator tip.
 7. The kit according to claim 5, further comprising atleast one cleaning agent.